53 Highland Drive
Monroe, CT 06468
East Village- 2 Beds
- 1.5 Baths
- 1,011 sqft
2 Beds
1.5 Baths
1,011 sqft
Local Information
-- mins to
Description
Welcome to High Meadows! Monroe's 55+ Community is located on the Eastern edge of Connecticut's Fairfield County! Miles away from the Housatonic River's historic Stevenson Dam. Short drive to the NY border 23 miles+/- of Brewster on CT-I-84 and only 46 miles +/- I-95. This is an END-UNIT 1 Bedroom with 1.5 bathroom condo that hasn’t hit the market in over 20 years! Additional finished upper and lower levels with mechanical room for plenty of storage/workshop space. Washer and dryer on the main floor. Attached 1 car garage with additional parking. Clubhouse. Close to restaurants, entertainment, family farms/wine vineyards, ice cream shops, retail/food shopping, health care facilities/gyms and so much more! Come live in Monroe - a small town with New England charm!
53 Highland Drive, Monroe, CT 06468 is a 2 bedroom, 2 bathroom, 1,011 sqft condo in East Village, built in 1995. It last sold for $374,000 on Jul 7, 2025 (10% above the $339,000 asking price). It is currently off market. The Trulia Estimate is $396,700, with a rent estimate of $2,876/month.
Home Highlights
Parking
1 Car Garage
Outdoor
Porch, Patio
A/C
Heating & Cooling
HOA
$489/Monthly
Price/Sqft
No Info
Listed
180+ days ago
Home Details for 53 Highland Drive
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Interior Details Basement: Partially Finished,Heated,Cooled,Storage SpaceNumber of Rooms: 4Types of Rooms: Master Bedroom, Bedroom, Bathroom, Dining Room, Family Room, Kitchen, Loft, Rec Play Room |
Beds & Baths Number of Bedrooms: 2Number of Bathrooms: 2Number of Bathrooms (full): 1Number of Bathrooms (half): 1 |
Dimensions and Layout Living Area: 1011 Square Feet |
Appliances & Utilities Appliances: Electric Cooktop, Electric Range, Oven/Range, Range Hood, Refrigerator, Dishwasher, Washer, Dryer, Electric Water HeaterDishwasherDryerLaundry: Mud RoomRefrigeratorWasher |
Heating & Cooling Heating: Forced Air,ElectricHas CoolingAir Conditioning: Ceiling Fan(s),Central AirHas HeatingHeating Fuel: Forced Air |
Fireplace & Spa No Fireplace |
Windows, Doors, Floors & Walls Common Walls: End Unit |
Levels, Entrance, & Accessibility Stories: 3Accessibility: Bath Grab Bars, Raised Toilet |
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Exterior Home Features Patio / Porch: Patio, Porch, EnclosedExterior: Rain Gutters, SidewalkNo Private Pool |
Parking & Garage Number of Garage Spaces: 1Number of Covered Spaces: 1No CarportHas a GarageHas an Attached GarageParking Spaces: 1Parking: Attached,Garage Door Opener |
Frontage Not on Waterfront |
Water & Sewer Sewer: Shared Septic |
Finished Area Finished Area (above surface): 1011 Square Feet |
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Year Built Year Built: 1995 |
Property Type / Style Property Type: ResidentialProperty Subtype: Condominium, ApartmentStructure Type: ApartmentArchitecture: Ranch,Apartment |
Building Building Name: High MeadowsConstruction Materials: Shingle Siding, Wood SidingNot a New ConstructionAttached To Another StructureDoes Not Include Home Warranty |
Property Information Not Included in Sale: Refer to Inclusion/ExParcel Number: 179229 |
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Price List Price: $339,000 |
Status Change & Dates Off Market Date: Wed Aug 23 2023Possession Timing: Withheld |
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MLS Status: Closed |
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Direction & Address City: MonroeCommunity: East Village |
School Information Elementary School: Per Board of EdJr High / Middle School: Per Board of EdHigh School: Masuk |
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Building Area Building Area: 1011 Square Feet |
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Community Features: Adult Community 55, Golf, Lake, Library, Medical Facilities, Park, Public Rec Facilities, Shopping/MallIs a Senior Community |
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HOA Fee Includes: Maintenance Grounds, Trash, Snow RemovalHas an HOAHOA Fee: $489/Monthly |
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BasementMls Number: 170591678Attic: Walk-up, Finished, StorageAbove Grade Unfinished Area: 1011 |
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HOA Amenities: Clubhouse,Management |
Last check for updates: about 3 hours ago
Listed by Stephen Thrower, (203) 543-3438
Realty ONE Group Connect, (203) 590-1111
Bought with: Marissa Papa, (203) 331-7043, Preston Gray Real Estate, (475) 269-5100
Source: Smart MLS, MLS#170591678

Price History for 53 Highland Drive
| Date | Price | Event | Source |
|---|---|---|---|
| 07/07/2025 | $374,000 | Sold | N/A |
| 10/20/2023 | $355,000 | Sold | Smart MLS #170591678 |
| 08/16/2023 | $339,000 | Listed For Sale | Smart MLS #170591678 |
| 05/10/1995 | $139,900 | Sold | N/A |
Market trends in Monroe
Last updated May 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
63
23MoM
Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | $6,818 |
| Assessment | $237,800 |
Home facts updated by county records
Comparable Sales for 53 Highland Drive
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.08 | Condo | $360,000 | 02/24/26 | 2 | 2.5 | 1,011 | |
0.16 | Condo | $329,900 | 01/06/26 | 1 | 1.5 | 1,011 | |
0.06 | Condo | $390,000 | 07/29/25 | 1 | 2.5 | 1,631 | |
0.14 | Condo | $362,000 | 09/26/25 | 1 | 1.5 | 2,011 | |
2.45 | Condo | $420,000 | 05/27/26 | 2 | 3 | 2,204 |
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